(R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid

Base Information

Chemical Name:(R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid
CAS No.:1605314-24-6
Molecular Formula:C₂₀H₃₂N₂O₇
Molecular Weight:412.483
Hs Code.:

Synonyms:(R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid

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Chemical Property of (R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid

Chemical Property:

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Technology Process of (R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid

There total 1 articles about (R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 6404-29-1
6-(tert-butoxycarbonylamino)hexanoic acid

: 1605314-24-6
(R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran / 0.25 h / -15 °C

1.2: 2 h / -15 °C

2.1: lithium chloride / tetrahydrofuran / 18 h / 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 °C

3.2: 5 h / -78 °C

4.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / 760.05 Torr

With palladium 10% on activated carbon; hydrogen; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate;
DOI:10.1002/ejoc.201301834

Reference yield: 66.0%

: 1605314-24-6
(R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid

: 100-51-6,185532-71-2
benzyl alcohol

: 1605314-26-8
benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

Guidance literature:: With diphenyl phosphoryl azide; triethylamine; at 20 ℃; for 3h; Reflux;
DOI:10.1002/ejoc.201301834

Reference yield:

: 1605314-24-6
(R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid

: 1265896-73-8
(R)-2-[(benzyloxycarbonylamino)methyl]-6-(tert-butoxycarbonylamino)hexanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine; diphenyl phosphoryl azide / 3 h / 20 °C / Reflux

2: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 0 - 20 °C

With lithium hydroxide monohydrate; diphenyl phosphoryl azide; dihydrogen peroxide; triethylamine; In tetrahydrofuran; water; 1: |Curtius Rearrangement;
DOI:10.1002/ejoc.201301834